Ethyl Acetate → HCID 57527200, compound

HRID 1452974Notes

Reaction equation

HRID 1452974 reaction equation
[CH:1]([NH:4][C:5]1[S:6][C:7]2[C:12]([N:13]=1)=[CH:11][CH:10]=[C:9]([C:14](OC)=[O:15])[N:8]=2)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O>C1COCC1>[CH:1]([NH:4][C:5]1[S:6][C:7]2[C:12]([N:13]=1)=[CH:11][CH:10]=[C:9]([CH2:14][OH:15])[N:8]=2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 57527204HCID 57527204, compound

Product 1

HCID 57527200HCID 57527200, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(isopropylamino)thiazolo[5,4-b]pyridine-5-carboxylate (1.67 g, 6.64 mmol, 1.0 eq.) in THF (17 mL) under nitrogen at 0° C. was added LAH (1M, THF; 10 mL, 10 mmol, 1.5 eq.). After 2.25 hr, ice and EtOAc were added, the cold bath was removed, and the solution was stirred to room temperature. The layers were separated, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel chromatography using CH2Cl2:MeOH (10:0.4) as eluent afforded (2-(isopropylamino)thiazolo[5,4-b]pyridin-5-yl)methanol as a white solid (1.25 g, 84% yield).

Workup

  1. customthe cold bath was removed
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6df157552a7844558adcfe05fde9d927
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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